Synthesis of an octahydroindolinone scaffold for a diversity-based chemical compound library

• Published in: Tetrahedron letters Vol. 48; no. 31; pp. 5411 - 5413
• Main Authors: Keaney, Gregg F., Johannes, Charles W.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 30.07.2007; Elsevier
• Subjects: Amaryllidaceae; Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; OXABICYCLIC ALKENES; DERIVATIVES; RING-OPENING REACTIONS; ALKALOIDS
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2007.06.018

The synthesis of a chemical compound library using diversity-oriented synthesis (DOS) is discussed. The library is structurally inspired by the Amaryllidaceae alkaloids, a family of natural products which has been known to demonstrate potent antiviral and antineoplastic activity. Highlights of this work include the rapid, high-yielding construction of the octahydroindolinone core and the solid-phase diversification of the lactam using a neutral phosphazene base. The synthesis of a chemical compound library using diversity-oriented synthesis (DOS) is discussed. The library is structurally inspired by the Amaryllidaceae alkaloids, a family of natural products which has been known to demonstrate potent antiviral and antineoplastic activity. Highlights of this work include the rapid, high-yielding construction of the octahydroindolinone core and the solid-phase diversification of the lactam using a neutral phosphazene base.